An optically active fluoroamine, which is the target of the present invention, is an important intermediate of pharmaceutical and agrichemical products. The direct production of the optically active fluoroamine is generally conducted by dehydroxyfluorination of a corresponding optically active amino alcohol in a protected amino form.
The present applicant has disclosed a process for producing an optically active fluoroamine by dehydroxyfluorination of an alcohol with the combined use of sulfuryl fluoride (SO2F2) and an organic base. This production process provides a target fluorinated compound (phthaloyl-protected form) with a yield of 23% in the case of using as a raw material an optically active amino alcohol of which the amino group (—NH2) has been protected with a phthaloyl group (cf. Scheme 1: Patent Document 1).

Further, there is known a process for dehydroxyfluorination of an optically active amino alcohol in a protected amino form using a fluorination agent known as Deoxo-Fluor™ (cf. Scheme 2: Non-Patent Document 1) or DAST (cf. Scheme 3: Non-Patent Document 2).


Patent Document 1: International Publication No. 2006/098444 (Japanese Laid-Open Patent Publication No. 2006-290870)
Non-Patent Document 1: Journal of Fluorine Chemistry (Netherlands), 2004, Vol. 125, P.1869-1872
Non-Patent Document 2: Journal of American Chemical Society (US), 1982, Vol. 104, P.5836-5837